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City Cast Chicago

City Cast Chicago

❄️ Make the most of December in Chicago

December 1, 2025 · — Emmi Mack

Hey friends! Feeling well-rested? Bright-eyed and bushy-tailed? Good, because winter is beginning in Chicago. Fear not, though! City Cast Chicago has you covered with seasonal hacks, events to hit, and stories to watch. On today’s episode, we give you our guide to December 👇

Podcast Player: "Your Guide to December 2025 in Chicago"
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What's CITY Talking About

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City Council previously rejected Mayor Brandon Johnson’s $16.6 billion city budget, which would have allocated $552.4 million to Chicago Public Schools. Now, as the budget battle continues, Board of Education members and teachers are voicing support for Johnson’s vision, saying it would prevent cuts at CPS. [Chalkbeat]

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Thanksgiving is over, but the spirit of gratitude is strong in this city. As we gear up for Christmas, here’s a list of more than 60 local nonprofits and mutual aid groups where your dollars can help provide food, clothes, and more to Chicagoans in need. [Block Club]

"Casino"
Robert De Niro and Sharon Stone in the 1995 film “Casino.” (Universal Pictures/Getty)

'Casino' Is Actually a Chicago Story

Martin Scorsese's classic “Casino” was inspired by the Chicago Outfit’s Las Vegas takeover during the ‘70s and ‘80s. The story was supposed to follow actual Chicago gangsters who oversaw Vegas operations … but studio lawyers put the kibosh on that. Here’s the real history. [Reader]

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Your Guide to Chicago in December 2025

Rudolph’s Bar
Grinch-themed cocktails from Rudolph’s Bar. (Emmi Mack / Hey Chicago)

Yes, it’s getting colder in Chicago. (As I write this, the wind is howling outside my window.) But December is jam-packed with so many events and spectacles, it’s not time to hunker down. Not yet.

Many (Many) Pop Ups

Pop-ups just feel like a party — whether it’s a bar or an artisan market. Lucky for us, December has plenty of both.

Some Holiday Pop-Up Experiences

Stay tuned in Hey Chicago for additional pop-up bars!

Upcoming Holiday Pop-Up Markets

State Street Macy’s
The State Street Macy’s is a classic Christmastime stop. (xetark / Flickr)

Winter Fun in the Loop

Don’t be a Scrooge — get down to the Loop this season and take in the holiday merriment.

There’s ice skating every day (weather permitting) at Millennium Park and Maggie Daley Park, but reservations are required. Reserve for Millennium Park here and Maggie Daley here.

Personally, I prefer the ribbon at Maggie Daley, although Millennium Park is home to Chicago's official Christmas tree. See it twinkling in McCormick Tribune Plaza.

Nearby, at the Macy's on State Street, catch window displays paying tribute to Marshall Field’s. Upcoming reservations to the Marshall Field’s Walnut Room (recently renamed) are full, but you can reserve a slot at the store’s Santaland here.

And, of course, there’s always the Christkindlmarket at Daley Plaza, now in its 29th season. The open-air market ends on Dec. 24. Theaters downtown are also bustling with holiday options:

"Dick Clark's New Year's Rockin' Eve" is also adding its first-ever Central time zone show this year, live from downtown. Hosts include Chance the Rapper and Ryan Seacrest ... will you be out there with them counting down?

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What To Do

Monday, Dec. 1

Tuesday, Dec. 2

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And now, I leave you with a poem: “Chicago and December” by W.S. Di Piero.

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